05. My favorite books of 2016

Posted 2016-12-29

Phew. Well, it’s been a while since I’ve had time to write, but the semester’s done, it’s the holiday season, and I have a chance to put down some thoughts. There’s tons I want to write about (huge financings in Latin America, the Red Compartida project finally awarded in Mexico). I’ll get back to these topics soon but today I just want to share some of the best books I read this year.

Readable telco

First off, ever since I read it a few months ago, I haven’t been able to stop thinking about The Master Switch. I originally got tipped off to it by Jonathan Libov in his post here, and I ate up this sometimes-dense but always-entertaining read in a matter of days. Tim Wu, a professor at Columbia Law School, does incredible work charting the rise and fall of connectivity networks (e.g., the telegraph, long-distance telephony, film, radio) and business and media empires (e.g., Western Union, AT&T, Hollywood) to understand what this history means for today’s giants like Google and Facebook. His central idea is that information platforms or networks start out as the playground of amateurs and hobbyists but eventually, through centralization and consolidation, come to be controlled by corporate interests and monopoly powers — a pattern so recurrent in history he dubs it “the Cycle.”

There are plenty reasons for the emergence of this dynamic (go read the book), but Wu’s thesis gets even more interesting when he asks if the internet, this century’s platform du jour, is more or less susceptible to this Cycle. The jury is still out, but the question is important, especially as we rely more on our information “pipes” and we start to realize how faulty our media might be. Wu’s historical evidence is compelling, and the narrative, seen through the eyes of multiple protagonists in business history, is a real page-turner, so I highly recommend The Master Switch.

On the same telco angle, Andrew Blum’s Tubes answers a really simple question very deeply: How does the internet physically work? That’s likely something that has only fleetingly crossed your mind, but the both global and local scale and macro- and nano- scope of the internet’s workings is truly fascinating. Blum reports from internet exchanges across the world, dives into the inner workings of the internet’s physical infrastructure, and even visits the home of the inventor of the internet, Vint Cerf. The book is a great read for anyone who wants to understand the internet’s physical infrastructure, but it’s also a great read for anyone who wants to understand the internet’s history and the people who built it.

Social science

So I’m hot off reading Michael Lewis’s The Undoing Project and I couldn’t have enjoyed it more. First, I’m a big Michael Lewis fan and his style. Here he does a fantastic job tracing the personal stories of Danny Kahneman and Amos Tversky, who together shape and influence the rise of behavioral economics (which in turn underpins a lot of Lewis’ other work like Moneyball and The Big Short). From an intellectual standpoint I was surprised the extent to which so much of what we discuss today in economics and psychology—heuristics, prospect theory, loss aversion—is actually just the work of this incredibly prolific pair. But just generally, I’m astounded by the personal lives of these two guys who have such unique personalities and incredible backgrounds (A Holocaust survivor? Combatants in multiple wars? An intellectual love affair?) that make for a great story.

If you’re into romance in the 21st century—and who isn’t?—I have to recommend two other social science-y titles. First, Aziz Ansari’s Modern Romance is a clever, insightful, and very funny look at dating practices in the U.S. and abroad. From ghosting to picking ideal first date spots, Aziz can pick apart modern courtship and ask just why we date the way we do. It isn’t the deepest or most analytical book, but it’s observant and funny. Honestly, I expected to hate the book since I’m not the biggest fan of Aziz’s comedy, but think he missed his true calling as a social scientist. This supports my theory that today’s most observant academics are comedians.

Similarly, Moira Weigel’s Labor of Love explores the rise of modern dating over the last century, and how capitalism and general market vocabulary have impacted our most intimate relationships. The text isn’t only thought-provoking in drawing the parallels between the commercial and the romantic, but it’s also an interesting history of the topic. (Did you know T.G.I. Friday’s started out as a singles’ bar? Me neither. But that’s hilarious.) Full disclosure: Moira’s a friend. She’s great. Buy her book.

Entrepreneurship stuff

Well I have not been able to stop thinking about Phil Knight’s memoir Shoe Dog, in which he chronicles his founding of Blue Ribbon Sports and later Nike, all the way from the initial idea to its eventual public offering. I’m not sure this story would have been as interesting told from any other perspective because Knight uncovers such personal insights about himself and plainly confesses how bad and often he fucked up. Most of all, it’s exciting to see this company constantly lurch from one catastrophe to the next… It makes you appreciate the thrill of building something new. I’m hoping this becomes required reading in some business school courses.

Another entry in the biography series: Dream Big, the story of legendary Brazilian investment firm 3G Capital and its founders. While the book itself I can’t say is particularly amazing, it’s hard to not appreciate the story: an ambitious young Brazilian named Jorge Paulo Lemann sets out to build a financial empire and, with a distinct management style, actually… succeeds. Just understanding this management philosophy is reason enough to check the book out. All this had added relevance after seeing AB InBev CEO and Lemann acolyte Carlos Brito speak at Wharton on leadership. His speech felt like a summary of this book, which to me offered further testimony of 3G’s philosophy.

Another great read on starting and scaling: Console Wars by Blake Harris charts the rise of Sega and Nintendo in the late ’80s into the early ’00s. As a former video game geek, reading exactly how Nintendo grew from a playing card company, to a mainstay in arcades, to a household name—and how Sega was determined to dismantle all of that—was so, so satisfying.

Oh, also, if you’re into the VC thing, make sure to pick up Venture Deals. It’s not necessarily the most riveting read, but it’s a great reference book to have. The authors, all big VC names, do an awesome job unpacking the major economic and control elements of a term sheet in most VC deals, explaining the typical organizational dynamics of firm, and highlighting potential financing challenges a startup might face at certain stages.


I spent a good portion of the year traveling as I’ve mentioned before, and along the way I picked up and read a few books on… travel. Both by Alain de Botton, they offer a new perspective that I think a lot of people sometimes take for granted.

First, The Art of Travel. What I like most about de Botton as a writer is that he takes deep philosophical interest in such small, seemingly inconsequential things. Here he asks, basically, why we travel for pleasure. What is it about us, and our daily lives, that makes the prospect of venturing somewhere exotic seem so enticing, or makes the memory of a trip so nostalgic? For people who consider themselves travelers, check this book out; it may make your next trip that much better.

Finally, I was excited to find and read the back cover of de Botton’s A Week at the Airport. The basic premise is that the author spends a week living in Heathrow Airport’s ultra-modern Terminal 5. Sounds terrible, but honestly I’ve always felt airports are a really strange but poetic place: neither here nor there, commonly hated but universally accepted, structurally ugly but in some ways kind of beautiful. de Botton, in his typically approachable philosophical style, unpacks a lot of this in his slim book. If you’re a traveler and hate your airport experience, or if you think there’s more to a given terminal than meets the eye, I recommend this quick yet intriguing read.